Chapter 21.SE, Problem 45AP

Give IUPAC names for the following compounds:

Interpretation Introduction

a)

Interpretation:

To identify the given compound by introspecting its structural formula and name it by the IUPAC system.

Answer to Problem 45AP

The IUPAC name of the given compound is p-methyl phenyl acet amide.

Explanation of Solution

The compound given is an unsubstituted amide that can be represented by the general formula ; since the amide nitrogen in NH₂ is not substituted by R¹ an alkyl group.

The R alkyl group attached to carbonyl carbon is phenyl, which has a para-substituted methyl with the substituent. ie

The IUPAC system of naming an amide unsubstituted follows this rule:

Replace the –oic acid or ic acid ending with amide and use the R alkyl group before this. Thus p-methyl-phenyl acetic acid to

Conclusion

Thus the IUPAC name of the given compound is p-methyl phenyl acet amide.

Interpretation Introduction

b)

Interpretation:

To identify the given compound by introspecting its structural formula and name it by the IUPAC system.

Answer to Problem 45AP

Thus the IUPAC name of the given compound is 4-ethyl-2-hexenoyl chloride.

Explanation of Solution

The given structure is consistent with , an acyl chloride.

The IUPAC system names an acyl chloride by first identifying the alkyl component R by its IUPAC name. [the parent hydro carbon residue]. Obviously this given the name of the parent carboxylic acid itself. Follow this name by replacing the -ic acid ending with oyl and finally add the halide suffix.

For the given compound the parent hydrocarbon R is a six-carbon unsaturated hydrocarbon chain as.

Thus this chain (longest chain) is named 4-ethyl-hexene-(2) [oic - acid] and the halide substituent chloride. We replace –oic acid by –oyl chloride. This leads to 4-ethyl-2 hexenoyl chloride or 4-ethyl-hexene-2-oyl chloride (from 4-ethyl-hexene-2-oic acid or 4 ethyl-2-hexenoic acid). The parent carboxylic acid.

Conclusion

Thus the IUPAC name of the given compound is 4-ethyl-2-hexenoyl chloride.

Interpretation Introduction

c)

Interpretation:

To identify the given compound by introspecting its structural formula and name it by the IUPAC system.

Answer to Problem 45AP

The IUPAC name of the given compound is thus dimethyl succinate.

Explanation of Solution

The given compound is

The structural formula A, of the given compound shows it to be the ester derivative of the dicarboxylic acid succinic acid is

The IUPAC system prescribes the following rule to name an ester derivative of a carboxylic acid thus:

First, identify the two alkyl group attached to each carboxylic oxygen (for two carboxylic acid groups in the given dicarboxylic acid). Then name the ester by starting with the name of their alkyl group (S) and adding the suffix–ate to replace the ending–ic acid.

Thus, combining these two rules, the given ester is named by IUPAC system as dimethyl succinate (from succinic acid) (for two CH₃ groups) attached to carboxyl-groups)

Conclusion

The IUPAC name of the given compound is thus dimethyl succinate.

Interpretation Introduction

d)

Interpretation:

To identify the given compound by introspecting its structural formula and name it by the IUPAC system.

Answer to Problem 45AP

Thus, the IUPAC isopropyl-3 phenyl pro panoate name of the given compound is isopropyl–3 phenyl propanoate.

Explanation of Solution

The structural formula for the given compound is consistent with the general formula for an ester derivative of a mono carboxylic acid is for the ester and for the parent acid the IUPAC system prescribes the following rules to name such an ester derivative is:

1) First, identify and name the alkyl group R¹, attached to the carboxyl oxygen. For the given compound, it is isopropyl

This corner in the prefix, first in the name of the parent carboxylic acid and also in the ester derivative.

2) Second, identify the R alkyl chain residue of the carboxylic acid. This for the given compound is the 3 carbon propanoic acid with a phenyl substituent at C-3 ie

3) Combining these two rules, finally the use the suffix–ate to replace the–ic acid ending. This given.

Conclusion

Thus, the IUPAC isopropyl-3 phenyl pro panoate name of the given compound is isopropyl–3 phenyl propanoate.

Interpretation Introduction

e)

Interpretation:

To identify the given compound by introspecting its structural formula and name it by the IUPAC system.

Answer to Problem 45AP

The IUPAC name of the given compound is N-methyl-4 bromo butanamide.

Explanation of Solution

The structural formula given for the compound is

Consistent with the general formula for an amide derivative of a carbonylic acid is with the amide bring further alkyl, R¹, substituted at the amide nitrogen ie NHR¹ or the IUPAC system prescribes the following ruler to name such substituted amides.

1) First, identify the N-alkyl substituent. In the given compound it is N-methyl-(mono substituted).

2) Next identify and name by the IUPAC system, the R, ie alkyl hydrocarbon chain component attached to the carbonyl carbon.

For the given compound, R is,

or remembering that carbonyl carbon is C-1, it is four carbon (longest hydro carbon chain) with a bromine at carbon-C-3. Thus, the name of this residue is 4-bromo butan–(derivative).

Finally, combining these two aspects, replace the–ic acid ending for the parent 4-bromobutanoic acid by –amide. This leads to N-methyl-4-bromo butanamide.

Conclusion

Thus the IUPAC name of the given compound is N-methyl-4 bromo butanamide.

Interpretation Introduction

f)

Interpretation:

To identify the given compound by introspecting its structural formula and name it by the IUPAC system.

Answer to Problem 45AP

The IUPAC name for the given compound methyl-1-cyclopentene carboxylate.

Explanation of Solution

The IUPAC system prescribes the following rules to name such compounds is:

a) First, identify and name the R¹, compound of the ester oxygen OR¹. This, in the given compounds is methyl –OCH₃.

b) Next identify the parent hydro carbon residue R attached the carbonyl carbon. For the given compound it is an unsaturated cyclopentene (5 carbon closed cyclic hydro carbon) with a double bond at C-1, which holds the carboxyl carbon. ie

Thus, this residue R is 1-cyclopentene for the parent acid 1-cyclopentene carboxylic acid. Finally, combining these two rules, replace the –ic acid ending by –ate ie carboxylate. Thus, the name of the ester is methyl-1-cycopentene carboxylate.

Conclusion

Thus the IUPAC name for the given compound methyl-1-cyclopentene carboxylate.

Interpretation Introduction

g)

Interpretation:

To identify the given compound by introspecting its structural formula and name it by the IUPAC system.

Answer to Problem 45AP

The IUPAC name of the given compound is phenyl-benzoate.

Explanation of Solution

The IUPAC system prescribes the following rules to name such esters is:

1) First identify and name the alkyl residue R¹ of the ester oxygen. This, in the given compound is phenyl Ph or (unsubstituted)

2) Second, identify and name by the IUPAC system the alkyl residue R attached to carbonyl carbon. This, in the given compound is

Finally combining these two rules, replace the –ic acid ending with the suffix –ate; the R¹ alkyl name is the prefix. This leads to phenyl-benzoate.

Conclusion

Thus, the IUPAC name of the given compound is phenyl-benzoate.

Interpretation Introduction

h)

Interpretation:

To identify the given compound by introspecting its structural formula and name it by the IUPAC system.

Answer to Problem 45AP

Thus the IUPAC name for the given compound is isopropyl-phenyl since it is a thio ester carbothioate.

Explanation of Solution

The IUPAC system prescribes the following rules to name such thiol derivatives (sulphur) is:

1) First, identify and name by the IUPAC system, the alkyl residue, R¹ attached to the –SR¹ function. For the given compound this is the iso-propyl function ie

2) Next, identify and name the alkyl R residue attached to the carbonyl carbon. This is, for the given compound

The parent carboxylic acid is thus phenyl carboxylic acid or

Finally, combining these two aspects, recall that the general ester of this carboxylic acid is the IUPAC name

Phenyl carboxylate for the this ester function, substitute the carboxylate ending by carbothioate. These the IUPAC name is, Isopropyl-phenyl carbothioate.

Conclusion

Thus the IUPAC name for the given compound is isopropyl-phenyl since it is a thio ester carbothioate.